This article examines notions of democracy in the writing of post-war literary identity, Nakai Hideo (1922–1993). Although Nakai is known as a fantasy novelist, tanka poet/editor and essayist, the focus text here is Kanata yori (From afar), a diary produced during the final stages of the war. Entries were largely written while the future literary identity worked as a mobilised student in the Ichigaya offices of the Imperial Army General Staff Headquarters. Audaciously, given the writer’s war-time role, the work was scathingly critical of the military policies of the time. While written in wartime, the diary was not published until 1971. This situates the work squarely in the politico-literary space of the post-war era. Furthermore, the diarist undoubtedly longs for a future without the militarist authorities. Brief reference is also made to a 1969 fantasy text, 'Kokuchō-tan' (Odyssey of the Black Swan), which features a young twenty-something protagonist whom Nakai identified as his own young post-war self. Both works present as fertile territory for an investigation of youth and democracy in post-war Japan.